


One Way To Graduate

by kittenofdoomage



Category: Supernatural
Genre: Alternate Universe, Double Penetration, F/M, Professor!Dean, Sex, Smut, Threesome
Language: English
Status: Completed
Published: 2017-07-13
Updated: 2017-07-13
Packaged: 2018-12-01 17:09:45
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,201
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11490873
Author URL: https://archiveofourown.org/users/kittenofdoomage/pseuds/kittenofdoomage
Summary: Professor Dean Winchester is hot. So is his brother. How does one celebrate leaving college?





	One Way To Graduate

This was where it started. Life. Becoming an adult.

And Y/N was terrified. Four years she’d been preparing for a career, and somehow she’d forgotten how to prepare for being a grown up. Now, there was precious little time to make plans for it - especially in her last class with Professor Winchester and his dreamy eyes, ridiculously good looks and tight, firm ass that you could bounce a quarter off.

“So this is it,” Professor Winchester announced, smiling as he leaned on the wide wooden desk with both arms, his biceps flexing in the short sleeved white shirt he wore, which was a little tight across his muscular chest. You could practically hear every woman in the room get wet.

Y/N focused her attention, listening to the professor and trying not think about his plump lower lip, how it would feel pressed against hers, if he would bit it when he came, or when she slipped her mouth over his thick, hard -

“- and we’re expecting to see all of you there.”

She blinked, looking to her side, where Mike was leaning on one arm, looking just at the professor with just as dreamy an expression as she expected she had. It wasn’t a stretch to guess her best friend was drooling over every aspect of the handsome professor as much as everyone else.

“What did he say?” Y/N hissed, and Mike sat up straight, smiling widely.

“I was talking about the charity graduation fair,” Professor Winchester called out with a grin, and Y/N slid down in her seat, clinging to her desk, her cheeks heating up a thousand degrees. “We’ve got alumni from all over coming down for it, it’s for a great cause, and I know you’re not gonna miss it, Miss Y/L/N, are you?”

“O-of course not, Professor.”

His grin grew and he nodded sharply, those intense eyes staring straight at her. “Brilliant.” Tearing his gaze away, he stood straight, gesturing to the entire class. “Well, it’s been an honor and a privilege, my young Padawans -” A collective giggle from the assembled students interrupted him, and he chuckled. “Go forth and make the world a better place.”

There was a cacophony of rustling papers and chair legs scraping against the floors as everyone picked up their things and made their way to the double doors at the rear of the auditorium. Y/N hung back, like she always did, not being a fan of crowds, and for a moment, she almost missed Professor Winchester calling her name. Turning to face him, Mike slipped past her, smirking as he wiggled his eyebrows at her.

“Yes, Professor?” she asked, clutching her folders to her chest as she approached the Professor.

“It’s Dean, Y/N, please. Class is dismissed, and you’ve technically graduated,” he turned away, rubbing the chalk from the board behind him as Y/N waited to find out what he wanted. “I really hope you’re gonna be at the fair later.” Her brow furrowed, and she kept her eyes on the back of his head, refusing to let her gaze drop to the way his ass fit perfectly in his tailored suit pants. The professor turned, his smile contagious as he looked at her. “I really would hate for you to miss it. My brother has flown in from Ohio to join me in the charity tandem bike ride.”

Y/N blinked. “Oh?”

Professor Winchester chuckled. “We’ve won the last three years running.”

“I, er, I don’t think I get where you’re going with this,” Y/N whispered, watching him as he walked around the desk, stopping directly in front of her, leaning his ass against the edge of the dark wood, folding his arms across his chest. Something pooled in her belly, and her heart thumped as she kept her eyes on his. “Sir?”

He groaned. “Please, don’t call me that.” His eyes sparkled as he kept staring at her. “It’s been hard enough all year seeing you sat in the front row with those little skirts on. You know, when you daydream, you tend to relax enough, give me a glimpse of the cute little panties you’re wearing.” He leaned forward as Y/N sucked in a harsh breath. “I especially love the Little Mermaid ones.”

“P-professor -” she stuttered, and he laughed again, shaking his head.

“Dean,” he corrected.

“This isn’t appropriate,  _ Dean _ ,” she continued, feeling her throat go dry. “I mean, you’re a teacher and -”

“And you graduated today. Maybe you haven’t been through the ceremony, but you’re not my student anymore.”

Y/N shook her head. “I don’t wanna get you in trouble,” she whispered.

“Are you gonna pretend you haven’t spent the last two semesters staring at my ass?” Dean grinned, standing straight, his hands falling to his sides as he drew a little closer, and Y/N just about forgot how to breath. “You daydream an awful lot, Y/N. And you and, Mike, is it?” She nodded. “You’re really not very quiet when you talk.”

“Prof - Dean -” It literally felt like the sahara desert in her mouth as she tried to clear her throat. “I don’t -”

“All you gotta do is come to the fair,” he interrupted. “I’m not gonna make you do anything you don’t wanna do, sweetheart. But I’m struggling to get you out of my head.” He was so close to her now, she could smell the mints on his breath, and feel the heat coming off of his body. One hand raised from his side, pushing a stray strand of hair from her eyes, tucking it behind her ear as she tried to remember how her lungs worked. “Just come to the fair,” he asked, and for a moment, Y/N thought he was going to kiss her.

Then he drew back and disappointment settled in her belly, alongside the burning arousal that had her imagination throwing all sorts of scenarios at her.

“Okay,” she breathed, unsure if the word even made sense. Dean pulled back, still smiling, an obvious tent in the material of his suit pants. “I’ll be there.”

“Good,” he replied, moving back around behind his desk. “I’ll look forward to it.”

*****

The sun was dipping over the horizon as Y/N parked her battered old Ford truck that she’d been struggling to keep alive since she was sixteen. It made a thunking clunking sound as she turned the engine off and applied the parking brake, and a sudden knocking on her window made her jump. Mike’s huge grin was at her window, a nervous looking junior behind him.

“Hey, sweetcheeks!” Mike called, and Y/N rolled her eyes, before grabbing her purse and climbing from the truck. “Didn’t think you were going to make it.” She tilted her chin upwards, and Mike clapped his hands together. “This is Denny. He’s my new beau.”

Her eyebrow arched as Denny gave her a little wave, and she wondered how long this “beau” would last. Mike was notorious for fucking his way through any class on campus, although now he’d graduated, he’d have to find a new pool of talent. Or he could hang around Stanford forever and continue to bang any guy that so much as twitched at swinging towards his gender.

“So, rides?” Mike interrupted her chain of thought, and Y/N smiled tightly.

“Actually, I wanted to go and watch the Alumni games. After all, we’re graduates now and we might have to compete next year.” The noise Mike made was scornful, and she eyed her best friend carefully. “You don’t have to come.”

“What she means by watching the Alumni games,” Mike started, leaning over to Denny like he were a fifth grader being taught about life, “is that she wants to watch Professor Winchester and his devilishly handsome brother in tight shorts on a tandem bike. Hence the short black number.”

Y/N felt her cheeks color, and she slapped at Mike’s shoulder, provoking an over the top laugh from him, and Denny smiled awkwardly. “Tell me again why you’re my best friend?”

“Because I would not judge you if you banged your Professor,” he retorted, and Y/N grit her teeth.

“I’m not a student anymore.”

“Hmmm.” Mike eyed her for a moment, before taking her arm, and looping his other through Denny’s, who followed his lead meekly. “Okay, we’ll walk you over to see the races. But then I’m getting this one on the helter skelter.” 

The crowds were already heaving, most of the new graduates heading towards the bars and rides, the Alumni games going mostly unattended. Professors filled the rows of seat, and Y/N picked the back row, settling down and steadfastly ignoring the way Mike immediately attached himself to Denny via the lips, making noises that had Mrs Torden from the Science Department tutting and glaring at them whilst thumbing the cross hanging around her neck.

Four races passed, and the lights of the small arena came on as the sun continued to lower. The relay race was triumphantly won by the Geology Alumnus team, which was surprising, but enjoyable to watch. Mike and Denny continued to make out on the bench beside Y/N, and she deftly avoided looking at them as she knew that her best friend had wandering hands that bordered on public indecency.

“And now, it’s the annual tandem alumni race,” the announced called, the sound fizzing through the ancient speakers. Y/N sat up a little straighter, ignoring Mike’s little cooing noise that was meant to mock her for her sudden interest. “Please welcome our champions, Dean and Sam Winchester!” Her eyes widened as the two brother emerged onto the track, the blue bike held in their hands. Both of them were wearing practically  _ sinful _ cycling shorts, smiling widely and damn, Winchesters apparently had good genes. Sam was every inch as good looking as his brother, even from a distance, and Y/N squirmed in her seat as they walked down the track with their backs to the crowd, admiring not one but two delectable derrieres.

“Damn girl, now I know why you wanted to watch,” Mike teased, breaking away from Denny’s mouth for all of two seconds before his tongue was once again locked against the junior’s. 

There were four teams altogether, but Dean and Sam sailed through it like they were pros. Both of them were laughing as they went round, alternating between taking the race seriously and swinging their legs out like children, and Y/N couldn’t take her eyes off of them. They were announced the winners for the fourth year running, and as they sauntered off with their prize, Dean looked up, catching Y/N’s eye, before nudging Sam, pointing her out to him. She could feel her cheeks heating up as the younger of the two smirked, nodding at his brother and saying something to him that made Dean laugh.

“We’re going,” Mike announced suddenly, pulling a flushed looking Denny up from his seat. “You good, Y/N?” She nodded dumbly, her eyes still on Dean and Sam as they walked through the crowd to the exit. In her purse, her phone buzzed, and she frowned, pulling it out.

_ Come meet us by the car park. D. _

It wasn’t unusual for a professor to have a student’s number, but Professor Winchester had never text her before, and she didn’t know who else it could be. The “us” made her both nervous and excited, and she didn’t even notice Mike looking over her shoulder. “Oooo, someone’s gonna get lucky. I want details.” His words were rushed, and Y/N pushed him away, scowling.

“You’re supposed to talk me out of this,” she admonished, making him smile.

“I know. I’m such a bad influence.”

“Get out of here,” she hissed, and Mike laughed loudly, before tugging Denny along with him, disappearing into the throng of the crowd before she lost sight of them altogether. For a few moments, she sat there, not sure what to do, nerves making her entire body vibrate. She felt like everyone was watching her, like everyone  _ knew _ what she was thinking, but in reality, no one had even noticed her.

Standing from her seat, she sidled along the bleachers, making her way to the steps, still feeling like she was being judged by everyone she passed. It made her footsteps quicker and lighter, and by the time she got to the bottom, where the next race was starting up, she was practically jogging to the exit, clutching her phone in one hand, sweat covering her brow as butterflies swarmed in her stomach.

Outside the arena, the crowds were a little more dispersed, most of the students and other attendees heading towards the carnival at the other end of campus. The car park was almost deserted, save for a few couples making out in their cars, and Y/N worried when she didn’t spot either of the Winchesters at the exit. She pushed through a group of football players that were drinking heavily, leering at girls wearing too little, and thankfully, they ignored her, parting as she moved through.

And there they were. Both men stood by an old classic black car, one Y/N recognised from around campus, knowing it belonged to the professor. He spotted her first, waving her over, a broad smile on his face. “Y/N!” he called, and she blushed, heading towards them with her chin tucked into her chest, trying to appear invisible lest anyone notice what she was doing.

“Aw, she’s shy,” Sam commented, a smirk on his face that may have belonged to the devil himself, and Y/N felt her knees go weak.

“Don’t be a dick, Sammy,” Dean chided, reaching out to loop an arm around her shoulders. “I’m glad you came,” he said, bending to place a chaste kiss to her cheek, and Y/N let out an involuntary whimper at the touch.

“So this is the girl you’ve been talking about?” Sam asked, his eyes sweeping over her like he was appraising cattle. “I can see why.”

If her blush got any deeper, her head might explode.

Dean chuckled, nodding. “Hell yeah. Almost lost my cool in several classes.”

“Are you sure you won’t get in trouble for this?” Y/N asked, raising her eyes to meet his. “I still don’t feel -”

“Honey, you’re a graduate. And Dean’s not about to risk his future or yours,” Sam interrupted, his face softening. “Don’t be afraid of us. Just go with it.” He stepped closer. “For the record, Dean’s been talking about you for months. Telling me how beautiful you are, how smart you are…” He reached out, tracing her face with one long finger, and she shivered at the touch, a flood of arousal feeling like it was soaking her panties.

Dean was standing a little more behind her now, his hand placed on her waist as Sam looked at her like he wanted to devour her. “Thing is, sweetheart,” he muttered, pulling her hair to one side. “Me and Sam… we share a lot of things.”

“Y-you do?” Where was her voice? That didn’t sound like her. She wasn’t meek and frightened, but with these two giant men crowding her in, she felt like prey to a pack of lions. In a very good way, but still…

Sam nodded, grinning as he looked around the parking lot. “We’re pretty public here, Dean. Maybe we should get out of here?”

“Only if she’s comfortable with it,” Dean replied, kissing a path behind Y/N’s ear, making her eyes flutter closed. She nodded briefly, taking short, shallow breaths as her now-former professor ground his hips into her ass. “You sure? Need to hear the words, baby.”

“Yes,” she breathed, unwilling to open her eyes in case she woke up and it had all been some kind of sexy dream. Sam’s fingers grazed her chin, and she felt Dean pull away, his hand taking hers. Her eyes opened, and she took in the sight of both men staring at her. “Yes, I wanna go with you.”

There was a joint groan between them, and Dean tugged on her hand, pulling her towards the car. Sam moved away, around to the passenger side, as Dean unlocked the door to the driver’s side, and motioned for her to climb in between them. It was a tight squeeze - both men were huge, even in the massive interior of the old car, but Y/N felt like she’d belonged there her entire life.

Dean lived a few blocks off campus, so the car ride was quick. The whole way, Y/N kept wondering if anyone had seen them, if there’d be gossip, and worry slowly began to creep its way up her spine. Sam’s arm dropped around her shoulders as Dean pulled off of the main college site, onto the residential streets, and Y/N shivered at the touch of his thumb on her bare shoulder.

“You really are sexy,” Sam purred, leaning in close, his other hand resting on her thigh, just above the knee. Y/N couldn’t help but swallow reflexively at his closeness, turning her head to look at him and finding his lips almost brushing hers. “Can I kiss you, Y/N?” She licked her lips, nodding and Sam wasted little time in moving against her, pressing their mouths together as Dean continued to guide the car down the road. Sam was gentle yet demanding, his tongue sliding against hers, his hand moving further and further up her thigh until the tips of his long fingers were pressing underneath the skirt of her dress, skating over the thin cotton of her panties. “Fuck, you’re warm,” he whispered, breaking away, lips swollen and turned upwards in a seductive smile.

“No fair, Sam,” Dean warned, his hand coming to rest on your opposing leg. He didn’t hesitate or take it slow like his brother, his hand immediately sliding up to where Sam’s already was, and the younger brother smirked, curling his fingers around to brush your folds through the cotton.

“Sam,” Y/N gasped, unable to stop her hips thrusting forward against their fingers.

Dean groaned deeply, and Sam chuckled, hooking his index finger into the elastic of your panties and pulling them to the side. “Is that better, Dean?”

“Fuck, yes,” the elder man growled, and Y/N found her lips taken by Sam’s once more, as Dean’s fingers spread her already drenched pussy lips. “So wet and warm,” he growled, keeping one hand so tightly on the wheel that his knuckles were white. “Got her goin’ real good, Sammy.”

Sam laughed against her mouth, tugging on her panties so Dean could get at her more, and his brother didn’t stop as he dipped the tip of one finger into her slick cunt. “Can’t wait to get you back to the apartment,” Sam whispered. “You like sucking dick, baby?” Y/N whimpered and nodded, finally gathering the courage to move her arm, reaching into Sam’s lap and brushing the solid definition of his cock through the cycling shorts. “Yeah, that’s it,” he groaned, shifting so she could access him better.

Dean’s fingers dipped further, until he could sink one into her pussy to the knuckle and Y/N released a keening sound that had Sam covering her mouth with his again, encouraging her to keep running her hand over his twitching length.

The car turned, and Dean pulled his hand away, leaving her feeling bereft and wanting. She managed to open her eyes and saw he’d pulled into a parking garage, which she assumed was attached to his apartment building. Sam drew back, grinning wickedly as Dean climbed out of the car. “We’re here.”

Y/N smiled, allowing him to assist her from the car, before the three headed towards the elevator. Both men flanked her like security for a celebrity, but she didn’t mind one bit. The elevator was already at the parking garage, and it was empty as they walked in, and Dean pressed the button for the fifth floor. As the door shut, Sam pressed up behind her, as Dean turned to face her face on, and within a second, she was crushed between them, Dean’s mouth hot and urgent as it claimed hers. Sam’s fingers were up her skirt, pushing her panties out of the way to get at her slick centre, and Y/N couldn’t help but whine into his brother’s mouth.

The elevator shuddered and stopped at the third floor, and the doors opened, prompting Dean to turn, acting as though he hadn’t been sucking her face off, greeting his elderly neighbour with a smile. Sam remained where he was, his hand out of sight but still up Y/N’s skirt, two fingers buried to the hilt inside her core. She bit her lip, watching the elderly woman amble to the other side of the elevator, feeling Sam’s fingers move. There was a smirk on Dean’s face, and Y/N struggled to hold in a gasp, making the old lady look at her curiously. 

“Are you okay, dear?” she asked, frowning. “You look a little flushed.”

Y/N gave her a shaky smile, nodding, and Sam leaned in, propping his chin on her shoulder and presenting his most charming smile. “She’s not from California. Heat’s been getting to her all day, hasn’t it baby?” She nodded, just as Sam dragged his fingers out of her and thrust them back in, making her entire body jerk.

The old lady smiled kindly. “Plenty of water, dear, that’s the trick. Maybe a lay down?”

“That’s the plan,” Dean offered, grinning widely.

The elevator shuddered again, and Y/N almost breathed a sigh of relief as the doors opened onto the fifth floor. Sam’s fingers abandoned her pussy, and she had to hold herself back from bolting as the old lady waved and bade her well. As soon as the doors were shut, both men burst out laughing, and Y/N scowled, slapping her purse into Sam’s shoulder, which only increased his mirth.

“You ass!”

“Oh, you loved it,” he replied, unable to stop smiling. Dean grabbed her around the waist, pulling her flush against him. 

“Sorry,” he whispered. “We can be a bit playful at times.” He bent his head, brushing his mouth against her neck. “Are we forgiven?”

Y/N made a small sound in her throat, before nodding and pushing him off. “I never thought you were…”

“Human?” Sam joked, and Dean’s fist flashed out and punched him in the arm, only making Sam start laughing again. “Sorry, dude, but it is hard to think of you as anything but cardboard in that suit.”

“He’s a good professor,” Y/N insisted, meeting Dean’s eyes and instantly blushing. “I mean, you are. I loved your classes. I just didn’t think you were so… fun.” He grinned, slipping his arm around your waist. “I didn’t mean to -”

“It’s a compliment,” he replied, cutting her off. “And I can show you exactly how much fun I am.”

She didn’t resist at all, only smiling coyly as Dean led her down the corridor to his apartment, with Sam taking up the rear. The younger man was still chuckling away to himself, but Y/N could feel his eyes on her ass, the feel of him still lingering on her pussy. There was no denying she wanted more - feeling the possibility of what was underneath the cycling shorts and shirt was making her knees quiver with anticipation.

Dean unlocked the door, holding it open as Y/N and Sam walked in, the latter immediately heading into the kitchen and grabbing a bottle of wine and some glasses. He waited for Dean to shut the door, and gestured to the bedroom. “I think maybe somewhere a little more comfortable than the couch?” he suggested, and Dean grinned at him, nodding.

“This way, sweetheart,” he said, the edge of his tone making Y/N’s legs shake. She walked ahead, moving into what she assumed was Dean’s room, judging by the size of it. In the center of the room stood a huge queen-sized bed, and Sam moved past the both of them to sit on the end, placing two of the three glasses on the floor while he tore the cork out of the wine with his teeth. Offering the first glass to Y/N, he waited for her to take a sip, as Dean peeled off his shirt. 

“Mmmm,” she whispered. “That’s really nice.”

“Fruity, huh?” Sam asked, and she nodded. “It’s one of Dean’s favorites. He doesn’t like much in the way of wine.”

“I prefer beer,” Dean shrugged, looking at Y/N as he hooked his thumbs into the elastic of the cycling shorts. “It’s no big deal.”

“Wine is more sophisticated,” Sam pointed out, filling the other two glasses and passing one to Dean. Y/N’s face fell as he paused to take the wine, not removing his shorts like she was expecting. The reaction didn’t go unnoticed, and Dean smirked widely.

“I’ll show you mine if you show me yours.”

For a split second, you could have heard a pin drop in the room, and Y/N hesitated, before boldness took charge. She placed her wine glass on the chest of drawers behind her, before turning to face Dean. Reaching down, she took hold of the hem of the short black summer dress she was wearing, tugging it upwards and over her head. When she could see again, Dean was grinning at her, and Sam was open mouthed with the wine glass at half mast.

“You’ve been having to concentrate on teaching with that in the same room?” Sam questioned, unable to tear his eyes away. “Dude, you have way more focus than I gave you credit for.”

Dean chuckled, placing his drink on the nightstand, before turning to look at Y/N, who was almost holding her breath. He placed his hands on his hips, sliding the tips of his fingers underneath the elastic waistband, almost framing his cock underneath the material, and Y/N suddenly forgot how to breath. Her eyes were fixated on the swelling length, seeing it fill out between his fingers, and when he moved, pushing the cycling shorts down over his thick thighs, she exhaled shakily, with a whimper that she didn’t mean to make. Dean grinned at her, standing in only his socks, his cock jutting proudly outwards.

Sam stood up, downing his wine in one go, and placing the empty glass next Y/N’s. “My turn,” he chuckled, dragging his shirt over his head.

If there was ever a case of not knowing where to look, this was it. Between the two of them, Y/N was fairly certain she’d died and gone to Dreamboys heaven, because finally seeing what was under Professor Winchester’s smart suits, and adding his brother to the mix was almost too much.

Where Dean was lean and toned, Sam was softer but no less muscular. He was wider than his brother, and his cock was maybe a couple of inches longer, but not as thick as Dean’s. His hips were more pronounced, where Dean had the sexy bow legged look, which was more evident as he moved towards her.

“Hey, we’re naked. Why aren’t you?”

Y/N looked down, seeing her bra and panties, and before she could react, Sam was behind her, his fingers deftly unhooking her bra and dragging it down her arms. As Dean approached, sliding his fingers into the sides of her panties, Y/N kicked off her ballet pumps, feeling hot all over, mewling as Sam’s cock bumped against the small of her back.

Dean dropped to his knees, taking her panties down to her ankles, and she shuddered as he leaned in, burying his nose in the juncture of her thighs. He hummed against her, his fingers pressing into her knees to make her part them. “That’s it,” he praised, and Y/N sank back against Sam’s firm chest, feeling his large hands hook around her to cup her breasts.

“Fucking beautiful,” Sam whispered, grazing his teeth over her earlobe, and she shuddered again, whimpering as Dean’s tongue slid through her folds, bumping up against her clit. “You ever been fucked by two guys at once, Y/N?”

“N-no,” she rasped back, shaking her head a little, feeling Sam laugh against her. “Never. I… oh, god -” Words became cries as Dean started to lick at her in earnest, sucking her clit into his mouth and trailing his fingers against her soaked hole.

“You wanna be fucked at the same time?” Sam continued, flicking his thumbs over her hardened nipples. “You ever been fucked up the ass?” The thought made a thrill jump through her nervous system, just as Dean sank two fingers into her pussy, curling them around. She came undone at the seams, only held up by Sam’s strong grip. “Oh, she likes the thought of that, big brother.”

Dean chuckled against her, not stopping his movement, and Y/N could feel his fingers pressing into the sweetest parts of her, making her walls clutch and contract around him. 

“I’ve… I’ve never had anyone that… that big there,” she whispered, as Sam’s hips rolled into her, reminding her of the size of his dick. “I… won’t it hurt?”

“Not if we prep you properly,” Sam replied, squeezing her tits hard. She yelped, feeling a rush of warm between her legs, and Dean groaned in ecstasy. 

“Fuck, Y/N…” He pulled back looking up at her with wetness coating his lips and chin. “You a fucking squirter?” Her eyes went wide; she’d never done that before, but then, no one had really done anything like this to her before. Every sexual encounter she’d had before this looked like a pre-watershed showing of The Brady Bunch - Dean and Sam were raising the bar to a point that she may never be satisfied again. Dean seemed to pick up on her apprehension, a smile stretching his lips wide. “Oh baby, have we got a treat for you.”

If this was the path to adulthood after college, you could sign her the fuck up.

Dean got to his feet, leaning in to kiss her hard and fast, leaving the lingering taste of her own pussy on her lips, and she couldn’t help but moan loudly at that. He tugged her backwards towards the bed, before laying across it, his head just at the edge. “Sit on my face,” he requested, and Y/N bit her lip, unsure. Sam placed a hand on her ass, encouraging her forward, and she hesitantly climbed onto the mattress, swinging her leg over Dean’s shoulders so she was facing Sam. Dean grabbed her ass, urging her upward until her pussy was hovering over his mouth, and then he dragged her down to plunge his thick tongue into her cunt.

The cry of shock that she gave was enough to have her lurching forward, and Sam was there to catch her, kissing her breathless as his brother worked her pussy over. Y/N moaned into his mouth, reaching between them to wrap her fingers around his thick cock. Sam grunted against her lips, pulling back to look into her eyes as he fucked into her hand. “Just like that…”

“Can I suck your cock, Sam?” she whispered, batting her eyelashes, the wine starting to have an effect on her. Y/N liked to think of herself as adventurous, but this was more than she’d ever imagined would happen to her. Sam’s face crumpled with pleasure as she swiped the pad of her thumb over the tip of his cock, and bent down, struggling to concentrate with Dean’s tongue lapping at her pussy, his nose buried in her mound.

The hiss Sam gave as her lips wrapped around his dick was reward enough, and Y/N closed her eyes as she sank down on him, ignoring the awkward angle she was at. Thankfully, Sam was tall enough that the position didn’t cause too much discomfort, but it was hard to keep her focus when Dean was edging her closer and closer to orgasm with his tongue, his fingers digging into her ass to hold her in place.

“Oh fuck, you’re good,” Sam growled, fisting his hand in her hair to hold her steady. “Can I fuck your mouth, baby? How much you think you can take of my big dick?” Y/N pulled back with a gasp, looking up at him with a sultry expression; if there was one thing she prided herself on, it was lack of gag reflex. Alcohol helped.

“Give me what you got, Sammy,” she purred, and he groaned, holding his dick with his thumb and forefinger to guide it back to her lips. He smeared the tip around her mouth, leaving precome on her face, before pushing between her plump lips, not stopping until he could feel the column of her throat constricting around him. Y/N moaned and wiggled, before drawing back a short way, and pushing back down, almost to the point that her nose was in his pubic hair.

The noise he made was guttural, and he didn’t hesitate to start pumping his hips back and forth, forcing more and more of his cock into her throat until it bulged with the width of him. Dean paused in his ministrations to look up, groaning at the sight of her taking every inch of his baby brother’s massive cock.

“Oh, Jesus, Sam…” he groaned, before adjusting himself to thrust two fingers into her soaked cunt. “Gonna make her fucking squirt while she’s deep throatin’ you.”

Sam could only nod in response, and by this point, his head was thrown back in pleasure. Y/N made a noise around him as Dean started to suck at her clit, using his tongue to stimulate the sensitive bud while his fingers curled and thrust into her. She raised one hand, cupping Sam’s balls and he snarled at the new move. When her index finger pressed into the sensitive spot just underneath his sac, he cussed loudly, giving a hard thrust, and Y/N lost all control.

Her eyes rolled back as she took Sam all the way, feeling him choke her, and her pussy spasmed around Dean’s fingers. Juices gushed from her pussy onto his face, and she vaguely heard him making encouraging statements, calling her sexy and gorgeous, but understanding English wasn’t her main priority with a cock in her throat and the most intense orgasm of her life reducing her to a quivering pile of skin and bones.

She barely acknowledged Sam withdrawing, holding her up as Dean slid out from underneath her. The mattress was firm but comfortable against her back, and both men watched as she panted out her exertion, and Sam exhaled hard.

“Man, you sure know how to pick ‘em,” he commented, lazily stroking his cock. “I coulda quite happily died with my cock in her throat.”

Dean grinned, eyes bright as Y/N pushed herself up, frowning at them. “Are you guys gonna fuck me or not?” she asked, and Dean couldn’t help but laugh at her bossy tone.

“Sure thing, darlin’,” he replied. “Where do you want us?”

She seemed to think about it, before a smile covered her face. “I want you in my -” The confidence faded - she’d never been very good at dirty talk, but Dean wasn’t about to let her get off that easy.

“Want me where?” he asked, leaning onto the bed and crawling up towards her. She swallowed, eyes wide as she looked at him.

“In my ass, Dean. I want you in my ass.” He groaned at the reply, and Sam chuckled, practically throwing himself onto the bed next to her.

“Does that mean I get your sweet little cunt?” he asked, dragging his fingertips down over her belly to stop just short of her pussy. She nodded, her bottom lip caught between her teeth as she looked at him. “Hmmm, tell me where you want me, baby.”

“In my… my cunt, Sam,” she breathed, seemingly growing a little more confident. “Want that thick cock of yours stretching me out.” He groaned, leaning in to kiss her as Dean made a little noise gathering what he needed. Two foil packets landed on the bed, and Y/N looked up to see the bottle of Astroglide in his hand. “I’m on birth control,” she whispered. “And I’m clean.”

Dean raised an eyebrow. “It’s up to you, sweetheart. We’re clean, and careful. If you don’t wanna use them -”

“No,” she stopped him, smiling. “Wanna feel  _ everything _ .”

“Oh fuck me,” Sam groaned, laying backwards on the bed. Y/N saw her chance and straddled him, rubbing her exposed pussy over his thick length, pressing it into his belly and leaving a trail of glistening come on his skin. “Oh fuck,” he repeated, and Y/N smiled.

“That’s the idea,” she chided, and Sam growled, reaching up to grab her. She shrieked as he pulled her down, unbalancing her position, and as she tried to readjust, he smashed their mouths together, using his free hand to line his cock up against her pussy. “Sam,” she mewled, the words lost between his lips, and he made a primal noise as the tip of his cock pressed between her walls.

“You have no idea how fucking hot that looks,” Dean drawled, moving himself behind Y/N as Sam let her take over, groaning as she sank down onto his thick cock. He barely managed to get the lube on his hand, unable to stop watching the way Y/N squirmed and mewled whilst impaled on his brother’s dick. “Jeez, she looks fucking stuffed, Sammy.”

Sam moaned in response, arching onto the bed as Y/N panted and squeezed her walls around his length, feeling him pressing into places she didn’t know she had, almost to the point of pain. As he started to thrust, she could feel Dean behind her, and she emitted a little squeak as two fingers brushed over her asshole, slick to the touch.

“Oh, you’re fucking tight there, aren’t you?” he muttered darkly, and Y/N nodded, panting, feeling more and more turned on by the thought of him touching her hole, and the second he pushed the tip of one finger in, she screamed, coming hard over Sam’s cock. Sam grunted, fucking up into her harder, the noises he made echoing around the bedroom. 

“Fuck, Dean, I’m not gonna last,” he warned and Dean nodded, pushing his finger further in as Y/N thrashed and whimpered, pushing back against him.

“More, Dean, please,” she begged, and he grinned, slowly sliding a second finger into her. She’d done this a few times before, and knew his cock would hurt, but the pain/pleasure threshold was becoming a blur and all she wanted was both of them, buried to the hilt inside her.

She was definitely ruined for anyone else after this.

Dean hesitated, still moving his fingers inside her, feeling the thick fullness of his brother’s cock through the thin wall, and he groaned, dropping his forehead to rest against her back. “Don’t wanna hurt you,” he whispered, and Y/N shook her head.

“You won’t. Please,” she pleaded again, “I need to feel you both. Wanna be stuffed with your cocks, filled with your come.”

Sam made a funny noise. “Oh god…”

The elder brother withdrew his fingers, and Y/N whined pitifully at the loss, until seconds later, she felt the bare, blunt head of his cock press against her ass. “Yesss,” she hissed, feeling the slight burn of the stretch as Dean slowly pushed forward. It took a second for the tight ring of muscle to give, and then he was sliding home, groaning deeply as her hot flesh surrounded him. The cry she gave only spurred him on, and he thrust hard, burying himself inside her, his balls resting against his brother’s.

“So full…” she whimpered, and Dean grunted in acknowledgement.  “Fuck me, please…” The words were so quiet, he might have missed them, and his eyes connected with Sam’s over her shoulder. His brother gave a sharp nod and a sly grin, and then they both moved.

Y/N was certain she’d died. Two huge cocks buried inside her, like a push and pull of magnificent proportions, filling her one at a time, brushing against each other with each stroke. It was a fire in her belly, expanding and pulsing, consuming her entire body until she felt like she was going to implode. White lights danced behind her eyelids - she couldn’t keep them open any more with such overwhelming pleasure.

Sam’s hand palmed her breasts as she bounced on his cock, the tightness of her cunt only increased by his brother’s dick in her ass. He knew he wasn’t going to last much longer, and he wanted one more orgasm out of her sweet pussy before he pumped her full of come. 

“Fucking… so tight,” Dean gasped, his hand holding onto her so tightly, he knew there’d be bruises. His knees were digging against Sam’s thighs but he didn’t seem to care as he kept up the pace. “Come for us, Y/N. Come with both our cocks in you.”

She nodded, gasping for breath, her body shaking and writhing between them, and he felt her ass constrict as Sam gave an almost-roar, his hips pumping wildly. Y/N screamed, her hands grabbing Sam’s where they were gripping her breasts, and Dean felt liquid slicking up his brother’s thighs. Warmth suffused him where Sam was pumping her full of hot sticky come, and he lost control, thrusting into her ass and holding himself flush as his orgasm came swiftly, come dribbling out around the sides of his cock and onto his sac.

None of them could move. Y/N slumped forward onto Sam, breathing erratically, sweat sticking her hair to her forehead. Sam’s eyes were closed, his chest heaving up and down, and Dean… Dean could feel his knees locking, his thighs cramping, and he needed to move before he passed out and crushed her.

With a deep groan, he moved, withdraw from her, prompting a little hiss of pain from the drained girl, and he couldn’t help but smile as he moved to the chest of drawers and grabbed a towel. As he cleaned himself up, Sam gently eased Y/N off his chest, rolling her onto her side where she lay splayed out, come dripping from both holes, and a satisfied smile on her face.

“I think we broke her,” Sam commented, taking the towel from his brother and climbing from the bed. Y/N giggled, and Dean grinned.

“Nah, she’ll recover,” he mumbled, walking around the bed as Y/N’s eyes fluttered open. She looked exhausted but sated, and she smiled up at him with bleary eyes. “You wanna rest?” She nodded, and he bent down, pressing a chaste kiss to her lips. “Probably a good idea. We’re nowhere near finished with you.”


End file.
